There are some places you can't help but fall in love with at first sight and return to year after year

We've chosen some of the world's most beloved (and touristed) destinations and, with the help of the best travel specialists in the business, have ferreted out their secrets, their treasures, their unmissable experiences. The result is a series of step-by-step trips that will surprise and delight those who've never been to the destination before ... or who have been a dozen times. Each of our highly detailed itineraries has been vetted and perfected by a Condé Nast Traveler editor, and each can be bought as is with just one phone call. Let the romance begin

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The Challenge

Trying to describe all the pleasures and prides of Tuscany–that fecund, almost ridiculously picturesque region of central Italy–would take more pages than a single issue of this magazine, and even then, we'd just scratch the surface. So visiting the area, whose capital is Florence and which contains a dazzling number of the world's iconic masterworks, as well as some of its most luscious wines and scrumptious foods, presents two unconquerable problems. The first is a surfeit of affection. Everyone loves Tuscany, so you will never be alone. But take heart: Do you think Goethe, Twain, and Stendhal (enthusiasts all) had those narrow streets to themselves? Going to Italy means joining a centuries-long roster of tourists. The second difficulty is one of time and endurance—there is no way to see all of the region’s sights, no way to linger over every masterpiece, no way to stroll every beautifully preserved hilltop town. Attempting to do so would take several lifetimes, and most of us have only a week or so.

The Solution

There are many ways to discover Tuscany, of course, but the most efficient, intimate, and unexpected is to use a travel specialist such as Maria Teresa Berdondini of Tuscany by Tuscans. She was skilled at negotiating the realities of visiting Italy and at arranging special experiences that are the stuff of every tourist’s fantasy. Together, we worked out an itinerary that shows off an essential Tuscany, one that reveals the best of the region's tastes, smells, and sights and will appeal to both the first- and fifteenth-time visitor. And while the latter may cry foul over what's not in the trip (no extended tour of the Duomo? No visit to the area's Etruscan ruins?), they'll also make discoveries about an area that, even after a thousand years and countless visitors, still has its secrets.

Sadly, Maria Teresa Berdondini died shortly after I finished writing this piece. She was a wonderful resource and generous travel guide, and I know that the many people she helped to see the best of her beloved Italy felt the same sorrow I did upon learning of her death. I hope that Berdondini would feel some comfort in knowing that another of our top travel specialists, Maria Gabriella Landers of Concierge in Umbria, is carrying on her legacy and will handle all bookings that result from this trip–one Maria's gift to the world, fulfilled by another Maria. For the Italians, who find poetry in the everyday, it seems an appropriate tribute.

**

Day 1: Florence**

You’re meeting your guide in the lobby at 9 a.m., but even late risers should feel refreshed: Your flight from New York City arrived in Florence last night around 6 p.m., so you were at the Palazzo Niccolini al Duomo (39–055–282412; doubles, $302–$428), an elegantly restored sixteenth–century 12–room palazzo, in time to flop into the wide bed for a good night’s sleep. Just make sure you begin your trip on a Monday: Many of the places you’ll see today are closed over the weekend.

Florence is perhaps best known for being the seat of Renaissance art, and rightly so: A greatest–hits collection of artists passed through its streets—Michelangelo, Leonardo, Botticelli, and Brunelleschi among them. And like most art–rich towns, this one is also a city of commerce or, to be more precise, a city where creativity and commerce met and one fed off the ambitions of the other. Unlike Milan, Italy’s banking capital, or Rome, its religious center, Florence was the place where the rich went to buy goods that would showcase how wealthy they were. Here were silk weavers and table makers, silver workers and leather toolers—merchants and artisans who also became wealthy and made Florence a city where art, in its many forms, could be found on any corner, in anyone’s home, and even on anyone’s back. It’s no surprise the Florentines have always taken shopping seriously.

Cheeses come with jellies (or mustards, as they're called here)

of whatever's in season: Pear is made into as spic that

glistens like a pale citrine.

This dedication is apparent at your first stop of the day, the Mercato Centrale near San Lorenzo , a five–minute stroll from your hotel. Downstairs are stalls—some of which, like Nerbone, have been operated by the same family since the 1800s—selling meats, pastas, and cheeses. Behind one glass–screened counter, pimply skinned guinea fowls wait to be cleaned; another is dedicated to the freshest horse meat. Upstairs are fruits and vegetables, their provenance prominently displayed. Eating local is a relatively new concept in American dining; for the Italians, it’s a way of life. Back downstairs, you’ll stop by one of the stalls, Baroni Alimentari, whose cheerful proprietors will have prepared a cheese and meats platter for you [Fig. 1]. You’ll also sample genuine balsamic—aged for 20 years, it’s velvety–rich, and so precious that it’s served by the drop. Ask owner Paola to tell you about the process of balsamic authentication; it says a lot about how seriously Italians take their artisanal traditions. By 10:30 or so, after loading up on a jar or two of decadent truffle–infused honey or a knot of truffle (if you have $127 to blow on 100 grams), it’s off via car to the Officina Profumo–Farmaceutica di Santa Maria Novella (16 Via della Scala; 39–055–216276), a five–minute drive away. En route, have your guide point out the fifteenth–century Della Robbia statues, with their distinctive blue–and–yellow glaze, protruding from the stone walls of the city. They are as good a reminder as any of how impossibly rich in art Florence is: Pieces that a museum in any other city would be thrilled to have in its collection are left to neglect. It also explains why the Italians can sound blasé about their riches: “We are overwhelmed by beauty here,” my guide said with a sigh.

Although the building, majestic with its high, vaulted ceilings and apothecary display cases, dates to 1612, the pharmacy was begun in 1221 by a group of Dominican monks. In the seventeenth century, Grand Duke Fernando I de’ Medici gave the brothers permission to start mixing scent and unguents for the public. (The monks had long been patronized by various members of the Medicis, most famous among them Catherine de’ Medici, for whom they made special perfumes. Later, of course, she became the queen of France and obsessed with poison, for which the monks must not be blamed.) There’s nothing like buying the pharmacy’s signature rosewater right at the source, but first you’re off for a private tour of the store’s back rooms. The pharmacy’s “secret room” was once a library whose shelves held all the monastery’s recipe and herbology books; the upper portion of its walls are covered with fourteenth–century frescoes by a contemporary of Giotto’s. Left undisturbed for years, they are still astonishingly vivid.

At 11:15, it’s time to continue your tour of the senses. A short drive brings you to a narrow palazzo, at the top of which sits the aerie of Lorenzo Villoresi (14 Via de’ Bardi; 39–055–2341187). A philosopher turned perfumer, Villoresi produces cult scents that are both complex and somehow instantly familiar. Even if you can’t afford a $6,000 custom scent—in a deliciously Proustian experience, Villoresi interviews his private clients about their favorite smells and memories, and creates a one–of–a–kind formula—it’s fun poking around his atelier, with its shelves of glass dropper bottles filled with raw ingredients and its warm air smelling faintly of patchouli.

A half–hour drive takes you to Fiesole, an Etruscan hillside town with views so picturesque—fields dotted with olive and cypress trees and houses stained Tuscan ocher—that you feel as though you’ve wandered into a cliché. Break for lunch at Fattoria di Maiano, a working farm with a small restaurant, Lo Spacio (11 Via Benedetto da Maiano; 39–055–599600; entrées, $19–$26), appended to its charcuterie. Before you eat (on the terrace if the weather’s nice), have your guide show you the beautiful decaying fresco Madonna della Misericordia, by Spinello Aretino, who was influenced by Giotto, in a quiet part of the grounds’ cloister.

Zaccaro has become an expert at restoring and re-creating

religious paraphernalia for what remains of Italy's Jewish

population; ask to see his fold-up menorah.

By 2:30 you’re back in Florence, crossing the Arno, the swift–moving, tea–colored river that bisects the city, into the neighborhood known (rather uninventively) as Oltrarno. Once a working–class area of narrow, gloomy buildings, Oltrarno has managed the neat trick of gentrifying while retaining not only its cozy local feel but also its artisans. Your first stop is the shop and studio of silversmith Donato Zaccaro (12–14 Rosso Sdrucciolo de’ Pitti; 39–055–212243), who became an apprentice when he was 15.

Next it’s off to visit a different kind of craftsman: the leatherworkers at the Scuola del Cuoio (16 Piazza Santa Croce; 39–055–244534), which occupies a former dormitory appended to the back of Santa Croce Church (yet another example of how in Italy, the business world and the Church have always walked hand in hand). Begun in the 1930s by current owner Laura Gori’s father and great–uncle as a school to teach orphaned boys a trade after World War II, it now maintains several master leatherworkers as well as students from Italy and abroad. In an age when much of the fine fashion and adornment work for which the country made its name is now outsourced (mostly to China), there’s something touchingly anachronistic about watching the Scuola’s silent, blue–jacketed artisans stamping a pattern into a flat disk of leather, and then pressing a sheet of precious gold–leaf into it with a hot iron.

Bags at the Scuola del Cuoio tend

toward the trad but can be

customized in different leathers

and exotic skins.

A short stroll from the Scuola brings you to the grand Piazza della Signoria, where an overzealous radical friar began the “bonfire of the vanities” in 1497, urging his followers to throw their possessions into the flames (a year later, he was immolated for being a heretic in this same square). Note the tower jutting from the Palazzo Vecchio, the crenellated bulwark before you (once the town hall, it is now a museum). If you look closely, you’ll see that the tower is in fact not centered within the structure. This is because, finished in a burst of medieval–era busyness in the fourteenth century, it predates the building itself. If you think Florence is crowded now, try to cast your mind back 500 years; space was at such a premium then that you built wherever you could, incorporating whatever could be repurposed. In front of the Palazzo Vecchio stands a familar–looking guy, but don’t get too excited; although Michelangelo’s David did in fact reside here in the piazza for some 370 years, it was moved to the Galleria dell’ Accademia in 1873. (This copy dates to 1910—you’ll see the real thing tomorrow.) Head to the Loggia dei Lanzi, the open–air gallery to the right of the square. Built in the late fourteenth century as a public assembly hall, the Loggia now houses an assemblage of sculptures, including Cellini’s bronze of Perseus holding the head of Medusa, her blood flowing from the stump of her neck in ropes.

The statue dominating the Piazza della Signoria is of

Cosimo I de'Medici, who was eventually grand duke of

Tuscany and the founder of the Uffizi.

A five–minute walk takes you to the Duomo, the city’s undisputed architectural masterpiece and icon, whose magisterial bulk—and, let’s face it, gaudiness, thanks to its nineteenth–century neo–Gothic facade of striped pink, green, and white marble—overshadows everything in the vicinity. But if the structure is awe–inspiring, it’s not exactly lovely, being the result of a 170–year, multigenerational collaboration. Although the view from the top of Brunelleschi’s dome is spectacular (the great architect himself never got to see it; he died 15 years before it was completed, in 1461), it’s recommended only if you’re willing to tolerate an hour–long wait, stifling heat, crowds, claustrophobia, and 463 steep steps. An equally impressive (and earthbound) sight comes in the form of the bronze doors on the north and east side of the eleventh–century Baptistery, which depict tableaux from the Old Testament and the life of Christ. They’re copies of the originals, whose completion cost their creator, Lorenzo Ghiberti, most of his adulthood. Since it’s early evening and the crowds are a little thinner, this is a good time to get a few up–close–and–personal shots of the Duomo itself, especially since it’s just a few hundred yards from your hotel.

Dinner tonight is at eight o’clock at Simon Boccanegra (124/r Via Ghibellina; 39–055–2001098; entrées, $15–$22), a classic Tuscan trattoria a seven–minute stroll from your hotel. Order whatever’s in season, and don’t have a cappuccino after dinner—only befuddled tourists do so post–noon.

Day 2: Florence

Embrace your addled body clock and slip out of the hotel at 6 a.m. for what may be your only chance to have the city to yourself. In the gray light, with the streets stripped of tourists, time seems to peel away, and suddenly you’re a Renaissance–era Florentine, readying yourself for a long day in your workshop. Cross Ponte alle Grazie and Via di San Niccolò to the Piazzale Michelangelo, which offers gorgeous views of Florence and the hills behind it; in summer, the stepped rose garden beneath the lookout will be in full, riotous bloom. The walk to and from may take about an hour, but it’s worth it; by 8 a.m. or so, the sun will be blazing and the Piazzale crammed with hawkers, tourists, and tour buses. On the way back, circumnavigate the mighty Duomo again or contemplate those Baptistery doors—you’ll even have time for a cappuccino and a pastry before meeting your guide at the hotel at 8:45.

If yesterday’s art tour began with Florence’s quotidian treasures, today’s starts with its superstars. The Uffizi (39–055–2388651) opens at 8:15, and by 9 a.m., when you arrive, the line will already stretch the length of the building. Your guide, however, will have reserved tickets, and after your bags are scanned and your camera stored (photographs are forbidden), you’ll be vaulting four flights of steep stairs for the second floor.

Guarding the entryway to the galleries are several busts and paintings of the Medicis, and although you’ll be itching to get to the icons, let your guide detain you to give you a brief history of this family, who were responsible not only for building Florence and shaping modern–day Tuscany but for commissioning many of the great treasures of art.

The medicis decided to open the Uffizi to the

public in 1591 (they had used it as office space),

in effect creating the first modern museum.

Once one of the richest and most pow- erful families in Europe, the Medicis— bankers by trade, despots by design, and tastemakers by ambition—have no con- temporary equivalent. To properly repli- cate their power, influence, and wealth, you’d have to combine the artistic patron- age of the Rubells or the de Menils with the business acumen of the Rockefellers, add the political savvy of the Kennedys and the brute force of perhaps the Sopra- nos, and you’d still fall short. Between their rise in the thirteenth century and their sudden fall in the seventeenth, when the line abruptly ended, the Medicis produced three popes, two queens, and many Florentine rulers, and they support- ed the work of Galileo, Michelangelo, Leonardo, and Botticelli—a veritable parade of geniuses. You will en- counter the work of various Medicis throughout this trip. The Uffizi itself, incidentally, was once the office of Cosimo I, the first grand duke of Tuscany.

Say good–bye to the Medicis for now and head into the famed U–shaped Eastern Corridor, whose ceilings dazzle with sixteenth–century frescoes. Begin with Room 2, which houses thirteenth–century paintings, in particular three spectacular canvases of the Virgin Mary by Duccio di Buoninsegna, Cimabue, and Giotto. Giotto (1267–1337) introduced to Italian art the idea of “intuitive perspective.” While to us the paintings look flat, their proportion disarmingly off, it was an invention that would change Western art forever. As you walk through these galleries, you’ll be able to appreciate how much of a science painting really is, each successive generation riffing on the innovations of the preceding.

Skip forward in time to Room 7, which contains two of the most famous examples of early Renaissance art: Paolo Uccello’s dark, moody, and muscular Battle of San Romano (1438–40; note the more sophisticated sense of perspective) and Piero della Francesca’s diptych portraits of Duke Federico da Montefeltro and his wife, Battista Sforza (1465–66). Della Francesca’s portrait is notable not only for the complexity and honesty of its vision but because it illustrates a key characteristic of Early Renaissance art: the birth of portraiture. But there would be no Michelangelo without Botticelli. On the way to view the master’s two greatest works, the Birth of Venus (1485) and Primavera (1478) in Rooms 10–14 (actually one large hall), take a detour into Room 8 to view Filippo Lippi’s Madonna with Child and Two Angels (c. 1465). Lippi was Botticelli’s teacher, and it was he who first gave the Madonna a face that showed emotion. He was also the first to depict a child—the baby Jesus—with a child’s face instead of an adult’s shrunk to size. Botticelli’s two famous paintings, familiar from countless T–shirts, are spectacular up close, and your guide will explain to you their iconography and the techniques that informed them. After a quick spin through the Michelangelo room, No. 25—to view his brilliantly colored Tondo Doni (1506) and Titian’s Venus of Urbino (1538)—your last room is No. 43, on the first floor, where you’ll find three icons crammed into one tiny gallery: Artemisia Gentileschi’s Judith Slaying Holofernes (1620–21) and two Caravaggios—the lush Bacchus (1595–1600) and the terrifying, spellbinding Medusa (1595). You’ll leave the Uffizi dazed and reluctant, but it’s already 11 and you need to escape while you can.

Orsanmichele offers an insider's view of the city: Before you

is the Duomo; behind you, rooftops bristle with satellite

dishes, laundry, and sun-drugged ctas

It’s a 15–minute walk to your next stop, Orsanmichele. Now a church, the structure was built in 1337 as a granary; the statues tucked into alcoves in the facade were commissioned by the city’s many guilds in the fourteenth century. (Although Orsanmichele had been closed to the general public for a while at the time of my visit, Maria Teresa Berdondini was able to arrange for me to enter the building.) In the first–floor museum, you’ll find the originals of all 14 guilds’ statues (those outside are replicas): Here is Saint Matthew, the patron saint of bankers, and Lorenzo Ghiberti’s Saint John the Baptist, the patron saint of wool merchants. The statues are the perfect illustration of how religion entwined with commerce and art here. Up a funicular staircase is an astonishing room, its walls set with small sculptures, with stunning views across the Old City. After descending the five flights of stairs, it’s off to lunch down the Via Dante Alighieri (yet another prominent Florentine), a charming, curving street. Gaze up at the sides of the buildings, which bear quotes from The Divine Comedy, and at the corner of Via del Proconsolo, look through the picture window to the right, where you can see unearthed Roman ruins. Just past the Bargello Sculpture Museum is lunch option number one: a stall selling fat tripe sandwiches. If you’d rather sit down, you’ll soon be at Santa Croce square, where the dining establishments are touristy but the views quintessentially Florentine. Grab a table at the best of the bunch, Ristorante Boccadama (25–6R Piazza Santa Croce; 39–055–243640; entrées, $15–$55), for a plate of penne with vibrant green pesto. After lunch, have a cup of what Florentines swear is the best gelato in town, at Vivoli (7R Via Isola delle Stinche; 39–055–292334; $2–$11 a cup).

By 2 p.m., you’re entering the Complesso di Santa Croce (39–055–2466105), in the piazza of the same name. Yesterday, you saw the back of the complex, but today you’re going into the church itself. Begun in 1294 by the Franciscans, it holds 176 tombs of some of the Renaissance’s most remarkable figures, all Florentine by birth or association: Ghiberti, Galileo, Michelangelo, and Machiavelli (ask your guide to tell you how the latter came back into fashion in the eighteenth century). And there’s even more geniuses under this roof—in the form of Donatello’s elegant, almost animate Crucifixion and Annunciation and Giotto’s two splendid frescoes, all in the first two chapels. Next head to the Sacristy, where to the left of the door you’ll see what’s purported to be a remnant of Saint Francis’s cloak. On the way out, have your guide point out the watermark on the building from the disastrous 1966 flood. The waters rose to almost five feet, and many of the city’s most important structures—Santa Croce, Santa Maria Novella, the Duomo—sustained major damage.

Cap your chocolate lesson with truffle shopping; the finest

have Tuscan-inspried flavors–rosemary and salt, lemon peel,

olive oil (best in November, during the pressing).

A five–minute walk returns you to the life of the profane with stops in two more of Florence’s hidden ateliers. At Mosaici di Lastrucci (9 Via dei Macci; 39–055–241653), artisans fashion chunks of raw stone—chalcedony, jasper, agate—into mosaics of such intricacy and subtlety that they can look like paintings from a distance. The contemporary work—faux pastoral scenes and city landscapes—lacks a certain aesthetic sophistication, but the eighteenth– and nineteenth–century–inspired decorative work is stunning. From here, it’s a three–minute hop to La Bottega del Cioccolato (50 Via de Macci; 39–055–2001609), one of the city’s premier chocolatiers.

Now it’s just before 5 p.m. and you’re off to your last sight of the day—but what a sight. Even though you have pre–reserved tickets, the line to the Galleria dell’ Accademia (39–055–2388609) creeps around the corner. However, it’s far better to come at the end of the afternoon (the Accademia closes at 6:50 p.m.): The crowds are thinner than at opening time (8:15 a.m.), and you won’t have to wait in line for more than a few minutes. The Accademia—part of which is an art school—is in many ways far less remarkable than other things you’ve seen. But in the second hall, past seven unfinished Michelangelo sculptures, is David himself. The 26–year–old Michelangelo coaxed his masterpiece, commissioned in 1501, from a leftover block of marble that had already been hacked away by two other artists. Although the sculpture—ringed by a clear plastic barrier since it was attacked by a hammer–wielding visitor in 1991—cannot be photographed and is perpetually thronged, it almost doesn’t matter. You find yourself circling it as if in a trance, lingering over how expressive David’s muscles are, what power they evoke. Have a seat at one of the benches to the rear of the sculpture, and take your time; the museum will start clearing out by 5:45 or so, and it’s only a seven–minute walk back to your hotel.

There's no pasta at Trattoria Cibero, but the secondi–like

chicken-and-ricotta meatballs in sweet tomato sauce–are

so good you won't miss it.

Dinner tonight is at eight o’clock at Trattoria Cibrèo (122R Via de Macci; 39–055–2341100; entrées, $8–$17), a spin–off of the flagship Cibrèo, and although its menu is only half as long and you might share a table, the food is the same as you’d be eating next door, only for half the price.

Day 3: Lucca

After two days of wall–to–wall tourists, you’re ready for a break, so your trip to Lucca, a fascinating town to the northwest of Florence, comes just in time. It’s a ten–minute walk along a traffic–choked road to the Stazione di Santa Maria Novella, where you’ll buy your ticket for the 9:08 a.m. train at one of the self–service kiosks facing the main lobby (don’t forget to validate it at one of the yellow boxes at the start of the tracks). An 80–minute ride (mostly through suburban wastelands, sadly) deposits you just outside Lucca’s walls. Built by the Romans in 180 B.C., the city is known for its wealth: The silk industry, which flourished here during the eleventh and twelfth centuries, gave birth to a healthy banking industry; today the city is the country’s largest producer of tissue paper. It’s also known for its independent streak (it was the first Tuscan city to embrace Christianity and remains the sole conservative city in famously liberal Tuscany) and of course the magnificent walls that embrace the city. Built in the sixteenth and seventeenth centuries to protect the citizenry against their pesky Florentine rivals, the walls never actually saw any action, and by the eighteenth century had become a public promenade, their bulwarks refitted as parks. Your guide, who will meet you at the station, will rent you bikes, and then you’ll be off, soaring high above Lucca (or so it will feel) atop the walls, which are beautifully shaded with leafy plane trees—a kindness for which we can thank Napoleon’s sister Elisa, who spent the early nineteenth century ruling over the city. Lucca’s walls have also kept urban sprawl out and preserved intact the city’s beautiful narrow byways and cobblestoned paths.

The wide sea of freshly mown grass at the base

of Lucca's walls was once a moat.

A leisurely half–hour or so later, you’ll be gliding downhill, toward the remains of a Roman coliseum dating to A.D. 70. The amphitheater, which originally held 10,000 people, was converted into a quarry during the city’s thirteenth–century boom years, and later—in one of countless examples of Italian architectural palimpsest—the town’s produce market. Forty years ago, the market moved out of Lucca; today, the ghost of the original space (only a portion of the walls remain) is a pleasant piazza with cafés and souvenir shops.

From here, you’ll take a short ride through the medieval heart of town, which is full of lovely antiques shops, to the most spectacular of the city’s 99 churches, the Duomo di San Martino. Although its thirteenth–century facade is impressive enough—note the friezes depicting tableaux of everyday life, a scene for each astrological symbol—the city’s real treasure is inside. According to legend, the Volto Santo di Lucca, the wooden Christ figure that resides within a small temple, was carved shortly after Jesus’ death by his contemporary Nicodemus, and brought to the city in the eighth century. Depicted with a long face and intense, fierce, dark eyes, he seems to bristle with life. Your guide will tell you about the Luminaria di Santa Croce, an annual rite in which Lucca’s most sacred relic is removed from its case and paraded with great solemnity through the candlelit streets of town.

After visiting Villa Reale's grotto, head for the lovely allée

edged with potted lemon trees (in bloom in late spring

or early summer).

After wandering through the hushed, darkened church—stop to admire Tintoretto’s wondrous Last Supper—hop onto your bike and pedal off for lunch at Buca di Sant’Antonio (3 Via Della Cervia; 39–058–355881; entrées, $10–$18), a simple trattoria whose signature dishes include braised rabbit with olives. If the weather’s nice, sit outdoors and enjoy one of the restaurant’s signature dishes of pasta and fresh game. By around 2:30 p.m., return your bike and drive ten minutes into the hill northwest of the town. For centuries, Lucca’s richer families escaped the heat by retreating to their summer villas, and after the repeal of a medieval–era luxury law—which safeguarded against any extravagant displays of new money—several of them built rather grand residences. In the early twentieth century, though, many of the estates were put up for sale, as was the case with your next destination, the Villa Reale (55014 Marlia; 39–058–330108). The present 45–acre property combines a sixteenth–century summer estate and the former summer palace of the bishops of Lucca; the two were bought and joined in 1805 by Elisa Baciocchi (née Bonaparte), and spent the next two centuries passing through various minor royals’ hands. You’ll see the seventeenth–century grotto, a small circular stage attached to a cool cave full of deliberately rough–hewn carvings. Here, guests would play water games—invisible fountains would spout jets of cool, minerally spray, and noblemen and –women would tumble over one another, clawing at each other’s damp, transparent clothes, and, well, you get the picture. Before you leave, ask your guide to turn on the taps, and watch as streams of water burble up from the floors and whoosh down from the ceilings—you’ll wish you could join in the fun. Next, continue toward the main house, where your guide will lead you to an entirely natural outdoor theater: a low hillock forms the stage itself, and carefully pruned tiers of box hedges create the wings and backstage.

The family still inhabits the Villa Torrigiani in

summer. You'll feel like a character out of Jane

Austen touring Lucca's estates.

You’ll be back in your car by about 3:20 p.m. for the 20–minute drive to the Villa Torrigiani (39–330–644–211), notable for the beauty of its wide, sloping lawn and for the borderline campiness of its interiors— especially the egomaniacal ceiling fresco in the great room, which looks more like something you’d find in a contemporary sports star’s pad than in a sixteenth–­century palace (if nothing else, it’s proof positive that time does not diminish bad taste). Still, the entire house is a fascinating time capsule, and the well–preserved objects on display (paintings, bedding, clothing, china) tell an interesting story about the lives of Tuscan nobility.

Catch the 6:32 p.m. train and you’ll be back in Florence just before 8 p.m. You’ll have a little time to rest before dinner tonight at Trattoria Omero (Via Pian dei Giullari Arcetri; 39–055–220053), across the river near the Piazzale Michelangelo.

Day 4: Chianti

Pack your bags and bid Florence good–bye—today you’re off to Chianti, the hilly region at the heart of Tuscany that is the birthplace of many an oenophile’s and gourmet’s dreams. First, though, a little retail self–indulgence: At 10 a.m., meet your driver outside your hotel for the half–hour trip to the Mall (8 Via Europa, Leccio; 39–055–8657775), a chic, well–edited complex with outlets of some of Italy’s best brands, including Armani, Fendi, Ferragamo, and Marni. After shopping, it’s another 40 minutes to Panzano in Chianti, home of the Fontodi winery (50020 Panzano in Chianti; 39–055–852005). The drive through undulating fields of olive groves—their leaves a silvery blur, and row upon row of neatly lashed grape vines, their tendrils a tender new green—is treat enough, one of those all too rare times when the reality of nature eclipses even the dearest–held imaginings.

If you like Fotondi's Flaccianello,

but it at the winery and have it

shipped home–it sells for more

than $80 a bottle in the States,

when you can find it.

Although the Fontodi estate is an ancient one, its current owners, the Manettis, have only been making wine here since the late 1960s. This isn’t a large outfit—the winery produces just 300,000 bottles a year—but as you’ll see (and taste) on your tour, the Manettis have been able to remain entirely dedicated to their enterprise by staying relatively small. After a walk through the winery’s bowels, including the dark, deliciously cool basement stacked high with French oak barrels, you’ll be ushered into a sunny room with sweeping views of the valley below for a tasting with Giovanni Manetti, who today runs Fontodi with his cousin Marco. Manetti, who in his grace, charm, and dark good looks embodies the archetypical Italian man, began working at the winery as a reluctant 16–year–old; today, his wines consistently earn high marks by Robert Parker, and Manetti is an expert on the intricacies of growing the region’s signature Sangiovese grapes (more than 90 percent of Fontodi’s crop). Not surprisingly, food production of any kind in Tuscany is serious business, and wineries hoping for a DOCG appellation (similar to the French AOC, a governmental authentication of place of origin) have to meet inflexible standards. A similarly high bar is set for any producer who claims to be organic—Fontodi earned its certification in 2008. You’ll taste two wines here: perhaps the 2005 Chianti Classico, a Sangiovese with a touch of cabernet sauvignon, and if you’re really lucky, the 2006 Flaccianello della Pieve, the estate’s much–lauded 100 percent Sangiovese Super–Tuscan, which lingers on the tongue like velvet.

It’s just before one o’clock by now, time for lunch in the small town of Greve, just below one of the many cozy fortified medieval villages that dot the countryside. You’ll make this short drive on the Chiantigiana, an ancient road leading from Florence to Siena, and one of the most picturesque you’ll ever enjoy: Each vista—hillsides braided with rows of grape vines, sentries of shaggy cypress trees—is more beautiful than the last.
Once in Greve, your first stop will be Antica Macelleria Falorni (71 Piazza G. Matteotti; 39–055–853029), a renowned artisanal butchery where, under eaves groaning with thick slabs of cured ham (the air will be redolent with the intoxicating hazelnut scent of dried pork fat), you’ll be treated to a salami tasting and will learn the difference between guanciale and capocollo. Sadly, it’s against the law to bring these delicious meats into the United States, but buy half a pound and head into one of the cheese shops across the square to stock up for tomorrow’s picnic lunch. Don’t gorge, though; today’s lunch awaits right across the street at the unassuming Nerbone (22 Piazza G. Matteotti; 39–055–853308; entrées, $12–$20), which serves excellent seasonal pastas.

In spring, the Villa Bordoni's walkways bustle with great

blowsy roses and clumps of lavender.

After a brief passeggiata—there are lots of little shops, including a superior wine store, Enoteca del Gallo Nero (8 Piazzetta Santa Croce; 39–055–853297)—it’s back in the car for the last brief drive of the day, to your hotel, the sixteenth–century Villa Bordoni (39–055–854–7453; doubles, $267–$375), just up the hill from Greve—ask for the room on the lower terrace; it’s the most private and has its own veranda. A cozy ten–room villa, the inn was restored in 2006 and retains much of its native character, from the subtly painted walls to the small but elegantly landscaped gardens. Take a walk down the dirt path that leads to the main road, where you’ll pass through a classic Tuscan landscape of fields lacy with Queen Anne’s lace, poppies, and tangles of wild mustard greens, but be back in the villa’s handsome dining room by 3:30 p.m. for your private cooking class. During your two–and–a–half–hour lesson, you’ll learn how to make four courses for the night’s menu, the most revelatory being the pasta. Like the pasta, everything in the kitchen is made from scratch (in summer, this might include leek–flecked risotto, or goat cheese paired with richly meaty chicken liver morsels), and later, when you’re dining alfresco under the lilac–streaked sky, you’ll feel as though you’re tasting familiar dishes and ingredients for the very first time.

Day 5: Siena

A climb to the top of any of San Gimignano's

towers is rewarded with big-sky views over the

soft green hills.

After a breakfast of pastries and meats and cheeses (the Bordoni’s spread is particularly generous), hit the road at 9 a.m. for the 45–minute trip to San Gimignano, one of the region’s most famous walled towns. Once an Etruscan settlement and, in the Early Middle Ages, an important pit stop for pilgrims making their way to Rome, the city fell into swift decline in the 1340s, when the Black Plague tore through Tuscany. Such neglect left San Gimignano’s narrow alleys intact and protected 14 of the original 72 towers—built as lookouts by wealthy families, they now loom over the landscape like something out of a fairy tale, and at this hour you’ve got them all to yourself.

By 10:30 a.m., meet your driver at the entrance to San Gimignano (no cars are allowed inside the walls) and continue on to Siena, which you’ll reach by 11:30 a.m. Of Tuscany’s many medieval towns, Siena must certainly be the best preserved—at times, it can feel like a spectacular stage set for all your Tuscan fantasies. A Roman settlement established in the first century B.C., Siena once enjoyed great wealth as a prominent city on the Via Romea, the pilgrims’ route to Rome. But although it was rich in talent—Europe’s first bank was established here, and the city’s storied university was one of the first in Italy to be publicly funded—it had no major industry (the lack of a waterway stunted its manufacturing capabilities). By the thirteenth century’s end, the long decline had begun.

Like San Gimignano, Siena was saved by its own obsolescence. Even the arrival of the Medicis in the 1500s, and the town’s inclusion into the duchy of Tuscany in 1559, had little effect on its physical and cultural character: The basic infrastructure, the local customs, and even the carefully cultivated sense of isolation are unchanged. The result is a city that feels distinctly other, and an unignorable regional pride.

The first stop of the day—where you’ll meet your local guide—is the Church of San Domenico, just inside the town’s perimeter. Built in the 1200s, at Siena’s apex, it was extensively renovated during World War II, and will seem, after the glorious excesses of Florence, somewhat mousy. However, you’re here to admire not the few uncovered frescoes but rather the relics of Saint Catherine, who was born in Siena in 1347 and remains its most exalted daughter. In medieval times, every church on the Via Romea that was worth its salt had a relic—since relics attracted pilgrims, and pilgrims spent money.

Your walk from the church to the center of the old city leads you up and down hilly cobblestoned pathways, over which drying laundry flaps like pennants. Virtually no cars are allowed on Siena’s streets—there’s neither room nor need for them (you could also argue that cars are anathema to Sienese existence; it wasn’t until the 1960s that the city was even connected to Florence by a highway). A pleasant 20–minute meander leads you to the Gothic Palazzo Pubblico, the town hall since the fourteenth century. The real attraction here is the large clamshell of a square that fronts the hall: the beautifully bricked Piazza del Campo. Twice a summer—on July 2 and August 16—ten horses gather for the Palio, a 700–year–old race between the city’s contrade, the 17 neighborhood guilds that have governed Siena since the Middle Ages. The entire center of the Campo is mobbed with people from all over Italy, who crowd into town to watch the riders take three furious, bareback, anything–goes laps around the square. The winner—and the winner’s sponsoring contrada—get year–round bragging rights.

The floor tableaux inside Siena's Duomo recall

oversized cartoons in their expressiveness and

clean modernity.

You’ll hear more of the various contrade and the Palio a little later, but for now it’s off to the thirteenth–century Duomo, with its fantastic modernist multicolored striped–marble facade. Once inside, head toward the thirteenth–century hexagonal pulpit, to the left of the nave; your guide will interpret for you the scenes and meaning of this richly symbolic and intricately engineered piece of medieval artistry. But while your instinct here will be to look up—at the stunning vaulted ceiling, painted the dreamy deep blue of a night sky and spangled with gold stars—you should also look down: The cathedral floor is adorned with sixteenth–century mosaics of biblical scenes done in pieces of red, yellow, black, and white marble that have been fitted together like a puzzle.

The final treat of the Duomo is the Piccolomini library, housing the church’s collection of rare manuscripts and illuminated books. The majority of the library was built in the early 1500s, but it was sealed from view and left virtually undisturbed until the 1800s—hence the depth of color, tone, and clarity in the gilded wall frescoes depicting the life of Pope Pius II.

Your next stop is right across the square from the Duomo: the lobby of the Santa Maria della Scala Museum Complex (39–0577–224811), just to the right of a gorgeously high–ceilinged library, its walls completely covered in frescoes of winged angels. A sprawling tenth–century complex, it’s now home to the Archaeological Museum, the Children’s Art Museum, and the Contemporary Art Center. But from the 1200s through the 1960s, much of this building was used as a hospital. For proof, watch the first few minutes of the short video—about the complex’s wholesale renovation in the 1970s—that plays in a loop on a monitor in the lobby. All of a sudden, a black–and–white image of the frescoed room to your left pops up (probably from the 1940s), but instead of books, the room is filled with patients in white–sheeted iron–frame beds, nurses in peaked caps bending over them. What an inspiring surrounding, one imagines, for the patients recuperating there!

The square outside Siena's Duomo is quietest around

lunchtime. Take advantage of the lull to snap some photos

and enjoy the (relative) calm.

If you’re an archaeology buff, explore the museum’s first–rate collection of Etruscan vessels and masks; otherwise, head back out to the Piazza del Duomo and enjoy the picnic you bought provisions for yesterday in Greve. Then it’s off to the back of the Complesso for a short, steep downhill walk (the same path Saint Catherine took on her way home after visiting the sick in the hospital some seven centuries ago) to the headquarters of the Goose contrada (13 Vicolo del Tiratoio; 39–0577–42209), one of the city’s oldest and most powerful.

The enduring influence and social dominance of the medieval contrade system is often offered as exhibit A of the Sienese’s stubborn idiosyncrasy. The contrada is a district, a neighborhood group, a collective, a miniature local government, a community, and, most of all, an identity, and it is difficult to overstate its importance in Sienese life. Each contrada maintains its own small cathedral, headquarters, kitchen, restaurant, and stable (for the Palio horses); and membership, while not required, is certainly expected of any self–respecting Sienese (members donate the funds to maintain their contrada’s headquarters and activities). All Sienese define themselves by their contrada first; everything else comes after—it’s as if the entire city were one big university with a particularly rich Greek life. (If a man from, say, the Porcupine contrada marries a woman from the Forest contrada, he’ll probably still root for the Porcupines during the annual Palio. And a contrada is not merely a function of geography: Someone born into the Giraffe contrada will always be a member, no matter if he picks up and moves into the neighborhood run by the Caterpillar contrada.)

Each contrada has its own scarf, worn

on holidays, on its patron saint's day,

and if it wins the Palio.

At the Goose contrada’s HQ—a sleekly renovated multistory space with an unremarkable exterior—there are two important things to see. The first is the chapel dedicated to Saint Catherine, herself a Goose and so, naturally, the contrada’s prize alumna. A statue of the saint is flanked by beautiful multicolored scarves bearing images of a goose, and the walls are covered with naive but spirited frescoes by a fifteenth–century Sienese artist (also a Goose, the headquarters’ caretaker is quick to inform you). Much of the rest of the building is dedicated to celebrating the contrada’s numerous Palio wins. The victorious contrada is always awarded a lovely banner designed and painted by an Italian artist, and the good people of the Goose have amassed a great number of these, as well as Palio ephemera and memorabilia from over the centuries. It’s a rare intimate glimpse of the town’s two defining passions—racing and birthright—and will leave you marveling at the Sienese citizens’ dedication to a social system that faded out across the rest of Italy sometime in the Late Middle Ages.

Antica Drogheria Manganelli's interior recalls an apothecary:

It has a series of small, glass-fronted drawers filled with

brightly wrapped candies. The grocery sells everything from

fruitcakes to sausages studded with white cubes of fat.

From here, it’s a brief walk to the charming main drag, the Via di Città, which has picture–perfect parallel rows of clothing boutiques, housewares stores, and food shops. Two establishments worth a few extra minutes are Siena Ricama (61 Via di Città; 39–0577–288339), whose owner re–creates, in embroidery, motifs and scenes from famous local frescoes on beautiful linen lamp–shades and cotton blankets, and Antica Drogheria Manganelli (71–3 Via di Città; 39–0577–280002), an old–fashioned grocery.

Given Poggio Antico's high altitude (1,476 feet

above sea level), it's no wonder the place offers

sweeping Tuscan views.

It’s now around 4:30 p.m. and, sadly, time to leave. Walk a few minutes back to the right–hand side of the Duomo, where your driver will be waiting for you for the hour–long ride to the village of Montalcino, above which sits Poggio Antico (53024 Montalcino; 39–0577–848044), one of the area’s premier Brunello producers. After a tour of the sunny, modern winery led by a member of the cheerful staff, you’ll have a chance to meet Paola Gloder, Poggio’s vibrant, highly charismatic young owner. The 45–year–old was fresh out of university when her father, a Milanese banker, announced that he wanted her to try growing wine on his newly acquired estate. Gloder threw herself into learning the art and business of winemaking, and 25–odd years later, is producing small batches of wines that regularly receive the highest accolades from Wine Spectator and other publications. Later, in a tasting at the property’s wine store—the Riserva is complex and surprising, while the 2006 Rosso di Montalcino is as bright as summer—you’ll be able to experience them for yourself. Stock up on the wines here; Poggio Antico doesn’t take Web orders, and the wines can be hard to find in the States.

After a fantastic creative–Tuscan dinner at Poggio Antico’s restaurant (39–0577–848044; entrées, $26–$60)—whose patio overlooks a classic landscape of vast, elaborately stitched quilts of low green hills—it’s a 90–minute car ride to the Villa Bordoni for one last night in this lush green valley. The next day, you’ll have time for a walk and breakfast before a car comes to fetch you for the 30–minute drive back to Florence, where you’ll board your flight home. But not without a promise to return.